US4619992A - 3-(β-aminoethyl)-4-cyano-isothiazolylazo dyes - Google Patents
3-(β-aminoethyl)-4-cyano-isothiazolylazo dyes Download PDFInfo
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- US4619992A US4619992A US06/710,993 US71099385A US4619992A US 4619992 A US4619992 A US 4619992A US 71099385 A US71099385 A US 71099385A US 4619992 A US4619992 A US 4619992A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0081—Isothiazoles or condensed isothiazoles
Definitions
- the present invention relates to compounds of the general formula I ##STR2## where R is hydrogen, C 1 -C 4 -alkyl or unsubstituted or substituted phenyl, R 1 is allyl, unsubstituted or substituted alkyl, cycloalkyl or aryl, R 2 is acyl, R 1 and R 2 , together with the nitrogen, form a saturated 5-membered or 6-membered ring or a diacylimide radical, and K is a radical of a coupling component.
- radicals R in addition to hydrogen, are butyl, propyl, ethyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl, nitrophenyl and, preferably, methyl.
- radicals R 1 are C 1 -C 8 -alkyl which may furthermore be interrupted by oxygen and substituted by C 1 -C 8 -alkoxy, phenoxy, phenyl or C 1 -C 8 -alkanoyloxy, and cyclopentyl, cyclohexyl, methylcyclohexyl and norbornyl, and phenyl which is unsubstituted or substituted by chlorine, methyl or alkoxy.
- radicals R 1 in addition to those stated above are: CH 3 , C 2 H 5 , C 3 H 7 , C 4 H 9 , C 6 H 13 , C 8 H 17 , C 2 H 5 OCH 2 CH 2 , CH 3 OCH 2 CH 2 CH 2 , C 4 H 9 OCH 2 CH 2 CH 2 , CH 3 CONHCH 2 CH 2 , C 2 H 5 OCOCH 2 , CH 3 OCOCHCH 3 , C 6 H 5 OCH 2 CH 2 , C 6 H 5 OCH 2 CH 2 OCH 2 CH 2 CH 2 , C 6 H 5 CH 2 , C 6 H 5 CH 2 CH 2 , ##STR3##
- R 2 is, for example, C 1 -C 10 -alkanoyl which may furthermore be substituted by alkoxy or phenoxy, or is cyclohexanoyl, or is benzoyl which is unsubstituted or substituted by chlorine, methyl or methoxy, or is C 1 -C 8 -alkoxycarbonyl, unsubstituted, N-monosubstituted or N,N-disubstituted aminocarbonyl or phenylaminocarbonyl or the corresponding alkyl-, aryl- or aminosulfonyl radicals.
- acyl radicals R 2 are CHO, ##STR4##
- the coupling components KH are derived from, in particular, the aniline, naphthalene or heterocyclic series.
- the coupling components KH are of, in particular, the general formulae ##STR6## where R 3 is hydrogen, alkyl, aralkyl or aryl, R 4 is hydrogen or R 5 , R 5 is unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aralkyl or aryl, R 6 and R 7 are each hydrogen, alkyl, alkoxy, phenoxy, halogen, alkylsulfonylamino, dialkylaminosulfonylamino or acylamino, R 8 is cyano, carbamyl, nitro or carbalkoxy and R 9 is unsubstituted or substituted phenyl, alkyl or aralkyl.
- radicals R 3 are methyl, ethyl, propyl, butyl, benzyl, phenethyl, phenyl, o-, m- and p-tolyl and o-, m- and p-chlorophenyl.
- radicals R 5 are C 1 -C 6 -alkyl which can be substituted by chlorine, bromine, hydroxyl, C 1 -C 8 -alkoxy, phenoxy, cyano, carboxyl, C 1 -C 8 -alkanoyloxy, C 1 -C 8 -alkoxy-C 1 -C 4 -alkoxy, benzoyloxy, o-, m- or p-methylbenzoyloxy, o-, m- or p-chlorobenzoyloxy, C 1 -C 8 -alkoxyalkanoyloxy, phenoxyalkanoyloxy, C 1 -C 8 -alkoxycarbonyloxy, C 1 -C 8 -alkoxyalkoxycarbonyloxy, benzyl-oxycarbonyloxy, phenethyloxycarbonyloxy, phenoxyethoxy-carbonyloxy, C 1 -C 8 -
- radicals R 5 are methyl, ethyl, propyl, butyl, pentyl, hexyl, allyl, methallyl, 2-chloroethyl, 2-bromoethyl, 2-cyanoethyl, 2-hydroxyethyl, 2-phenyl-2-hydroxyethyl, 2,3-dihydroxypropyl, 2-hydroxypropyl, 2-hydroxy-butyl, 2-hydroxy-3-phenoxypropyl, 2-hydroxy-3-methoxypropyl, 2-hydroxy-3-butoxypropyl, 3-hydroxypropyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-butoxyethyl, 2-phenoxyethyl, 2-phenoxypropyl, 2-acetoxyethyl, 2-propionyloxyethyl, 2-butyryloxyethyl, 2-isobutyryloxyethyl, 2-methoxymethylcarbonyloxyethyl,
- radicals R 6 and R 7 are hydrogen, methyl, ethyl, propyl, bromine, chlorine, methoxy, ethoxy, phenoxy, benzyloxy, C 1 -C 6 -alkanoylamino, benzylamino and C 1 -C 4 -alkylsulfonylamino and -dialkylaminosulfonylamino.
- radicals R 8 in addition to those stated above are aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, ethylaminocarbonyl, diethylaminocarbonyl, methoxycarbonyl, ethoxycarbonyl, n- and isopropoxycarbonyl, n-, iso- and sec.-butoxycarbonyl, methoxyethoxycarbonyl, ethoxyethoxycarbonyl, n- and isopropoxyethoxycarbonyl and n-, iso- and sec.-butoxyethoxycarbonyl.
- R 9 is, for example, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonylmethyl, cyanomethyl, benzyl or phenyl which is monosubstituted or polysubstituted by C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy, phenoxy, benzyloxy, phenyl, chlorine, bromine, nitro, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -mono- or di-alkylamino, C 1 -C 4 -alkoxyethoxy, C 1 -C 4 -alkyl- or phenylmercapto or C 1 -C 5 -alkanoylamino, such as acetylamino, propionylamino, butyrylamino or valerylamino.
- the compounds of the formula I have yellow to blue hues and are particularly suitable for dyeing polyesters, nylons, cellulose esters and blends of polyesters and cellulose fibers.
- the dyeings obtained generally have good fastness properties, particularly on polyesters.
- the compounds of the formula I can be prepared by reacting a diazonium compound of an amine of the formula ##STR7## with a coupling component of the formula
- Preferred coupling components K 1 H are: ##STR9##
- the resulting diazonium salt solution was run slowly into a mixture of 12.8 parts of 4-phenyl-2-(N-diallylamino)-thiazole, 20 parts of acetic acid, 250 parts of water, 250 parts of ice and one part of amidosulfonic acid.
- the dye was filtered off under suction, washed neutral and dried at 50° C. under reduced pressure to give 18.0 parts of the dye of the formula ##STR10##
- This dye dye s polyesters in deep violet hues which have good lightfastness and fastness to dry heat pleating and setting.
- the resulting diazonium salt solution was run slowly into a solution of 3.9 parts of N-cyanoethyl-N-ethyl-m-toluidine in a mixture of 50 parts of water, 200 parts of ice, 10 parts by volume of 32% strength hydrochloric acid, 20 parts by volume of dimethylformamide and 0.5 part of amidosulfonic acid.
- the dye was filtered off under suction, washed neutral and dried to give 9.2 parts of the dye of the formula ##STR50## This dye dyes polyester fibers in clear bluish red fast hues.
- the compounds below can be prepared by a similar method.
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Abstract
A compound of the formula: ##STR1## where R is hydrogen, C1 -C4 -alkyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl or nitrophenyl; R1 is allyl, C1 -C8 -alkyl, C1 -C8 -alkyl substituted by C1 -C8 -alkoxy, phenoxy, phenyl or C1 -C8 -alkanoyloxy, cyclopentyl, cyclohexyl, methylcyclohexyl, norbornyl, phenyl or phenyl substituted by chlorine, methyl or alkoxy; R2 is C1 -C10 -alkanoyl, C1 -C10 -alkanoyl substituted by alkoxy or phenoxy, cyclohexanoyl, benzoyl, benzoyl substituted by chlorine, methyl or methoxy, C1 -C8 -alkoxycarbonyl, aminocarbonyl, phenylaminocarbonyl, CH3 NHCO, C2 H5 NHCO, C3 H7 NHCO, C4 H9 NHCO, (CH3)2 NCO, CH3 SO2, C6 H5 SO2 or p--CH3 --C6 H4 --SO2 ; or R1 and R2, together with the nitrogen atom, form a ring system, and K is a radical of a coupling component. The isothiazolylylazo compound of the invention is useful for the dyeing of the polyesters, nylon, and cellulose esters.
Description
The present invention relates to compounds of the general formula I ##STR2## where R is hydrogen, C1 -C4 -alkyl or unsubstituted or substituted phenyl, R1 is allyl, unsubstituted or substituted alkyl, cycloalkyl or aryl, R2 is acyl, R1 and R2, together with the nitrogen, form a saturated 5-membered or 6-membered ring or a diacylimide radical, and K is a radical of a coupling component.
Specific examples of radicals R, in addition to hydrogen, are butyl, propyl, ethyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl, nitrophenyl and, preferably, methyl.
Examples of suitable radicals R1 are C1 -C8 -alkyl which may furthermore be interrupted by oxygen and substituted by C1 -C8 -alkoxy, phenoxy, phenyl or C1 -C8 -alkanoyloxy, and cyclopentyl, cyclohexyl, methylcyclohexyl and norbornyl, and phenyl which is unsubstituted or substituted by chlorine, methyl or alkoxy.
Specific examples of radicals R1 in addition to those stated above are: CH3, C2 H5, C3 H7, C4 H9, C6 H13, C8 H17, C2 H5 OCH2 CH2, CH3 OCH2 CH2 CH2, C4 H9 OCH2 CH2 CH2, CH3 CONHCH2 CH2, C2 H5 OCOCH2, CH3 OCOCHCH3, C6 H5 OCH2 CH2, C6 H5 OCH2 CH2 OCH2 CH2 CH2, C6 H5 CH2, C6 H5 CH2 CH2, ##STR3##
In the case of radicals which can occur in isomeric form, the n-, iso- and tert.-compounds are all embraced by the abbreviated formula.
R2 is, for example, C1 -C10 -alkanoyl which may furthermore be substituted by alkoxy or phenoxy, or is cyclohexanoyl, or is benzoyl which is unsubstituted or substituted by chlorine, methyl or methoxy, or is C1 -C8 -alkoxycarbonyl, unsubstituted, N-monosubstituted or N,N-disubstituted aminocarbonyl or phenylaminocarbonyl or the corresponding alkyl-, aryl- or aminosulfonyl radicals.
Specific examples of acyl radicals R2 are CHO, ##STR4##
R1 and R2 together with the nitrogen form, for example, the following radicals: ##STR5##
The coupling components KH are derived from, in particular, the aniline, naphthalene or heterocyclic series.
The coupling components KH are of, in particular, the general formulae ##STR6## where R3 is hydrogen, alkyl, aralkyl or aryl, R4 is hydrogen or R5, R5 is unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aralkyl or aryl, R6 and R7 are each hydrogen, alkyl, alkoxy, phenoxy, halogen, alkylsulfonylamino, dialkylaminosulfonylamino or acylamino, R8 is cyano, carbamyl, nitro or carbalkoxy and R9 is unsubstituted or substituted phenyl, alkyl or aralkyl.
Specific examples of radicals R3, in addition to those stated above, are methyl, ethyl, propyl, butyl, benzyl, phenethyl, phenyl, o-, m- and p-tolyl and o-, m- and p-chlorophenyl.
Examples of radicals R5, in addition to those stated above, are C1 -C6 -alkyl which can be substituted by chlorine, bromine, hydroxyl, C1 -C8 -alkoxy, phenoxy, cyano, carboxyl, C1 -C8 -alkanoyloxy, C1 -C8 -alkoxy-C1 -C4 -alkoxy, benzoyloxy, o-, m- or p-methylbenzoyloxy, o-, m- or p-chlorobenzoyloxy, C1 -C8 -alkoxyalkanoyloxy, phenoxyalkanoyloxy, C1 -C8 -alkoxycarbonyloxy, C1 -C8 -alkoxyalkoxycarbonyloxy, benzyl-oxycarbonyloxy, phenethyloxycarbonyloxy, phenoxyethoxy-carbonyloxy, C1 -C8 -alkylaminocarbonyloxy, cyclohexyl-aminocarbonyloxy, phenylaminocarbonyloxy, C1 -C8 -alkoxy-carbonyl, C1 -C8 -alkoxyalkoxycarbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenoxy-C1 -C4 -alkoxy or phenethyloxy-carbonyl, and phenyl, benzyl, phenethyl and cyclohexyl.
Specific examples of radicals R5 are methyl, ethyl, propyl, butyl, pentyl, hexyl, allyl, methallyl, 2-chloroethyl, 2-bromoethyl, 2-cyanoethyl, 2-hydroxyethyl, 2-phenyl-2-hydroxyethyl, 2,3-dihydroxypropyl, 2-hydroxypropyl, 2-hydroxy-butyl, 2-hydroxy-3-phenoxypropyl, 2-hydroxy-3-methoxypropyl, 2-hydroxy-3-butoxypropyl, 3-hydroxypropyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-butoxyethyl, 2-phenoxyethyl, 2-phenoxypropyl, 2-acetoxyethyl, 2-propionyloxyethyl, 2-butyryloxyethyl, 2-isobutyryloxyethyl, 2-methoxymethylcarbonyloxyethyl, 2-ethoxymethyl-carbonyloxyethyl, 2-phenoxymethylcarbonyloxyethyl, 2-methoxycarbonyloxyethyl, 2-ethoxycarbonyloxyethyl, 2-propoxycarbonyloxyethyl, 2-butoxycarbonyloxyethyl, 2-phenyloxycarbonyloxyethyl, 2-benzyloxycarbonyloxyethyl, 2-methoxyethoxycarbonyloxyethyl, 2-ethoxyethoxycarbonyl-oxyethyl, 2-propoxyethoxycarbonyloxyethyl, 2-butoxyethoxy-carbonyloxyethyl, 2-methylaminocarbonyloxyethyl, 2-ethyl-aminocarbonyloxyethyl, 2-propylaminocarbonyloxyethyl, 2-butylaminocarbonyloxyethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 2-propoxycarbonylethyl, 2-butoxy-carbonylethyl, 2-phenoxycarbonylethyl, 2-benzyloxycarbonyl-ethyl, 2-β-phenylethoxycarbonylethyl, 2-methoxyethoxy-carbonylethyl, 2-ethoxyethoxycarbonylethyl, 2-propoxy-ethoxycarbonylethyl, 2-butoxyethoxycarbonylethyl, 2-phen-oxyethoxycarbonylethyl and 2-benzoylethyl.
Examples of suitable radicals R6 and R7 are hydrogen, methyl, ethyl, propyl, bromine, chlorine, methoxy, ethoxy, phenoxy, benzyloxy, C1 -C6 -alkanoylamino, benzylamino and C1 -C4 -alkylsulfonylamino and -dialkylaminosulfonylamino.
Examples of radicals R8 in addition to those stated above are aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, ethylaminocarbonyl, diethylaminocarbonyl, methoxycarbonyl, ethoxycarbonyl, n- and isopropoxycarbonyl, n-, iso- and sec.-butoxycarbonyl, methoxyethoxycarbonyl, ethoxyethoxycarbonyl, n- and isopropoxyethoxycarbonyl and n-, iso- and sec.-butoxyethoxycarbonyl.
R9 is, for example, C1 -C4 -alkyl, C1 -C4 -alkoxycarbonylmethyl, cyanomethyl, benzyl or phenyl which is monosubstituted or polysubstituted by C1 -C10 -alkyl, C1 -C10 -alkoxy, phenoxy, benzyloxy, phenyl, chlorine, bromine, nitro, C1 -C4 -alkoxycarbonyl, C1 -C4 -mono- or di-alkylamino, C1 -C4 -alkoxyethoxy, C1 -C4 -alkyl- or phenylmercapto or C1 -C5 -alkanoylamino, such as acetylamino, propionylamino, butyrylamino or valerylamino.
The compounds of the formula I have yellow to blue hues and are particularly suitable for dyeing polyesters, nylons, cellulose esters and blends of polyesters and cellulose fibers. The dyeings obtained generally have good fastness properties, particularly on polyesters.
The compounds of the formula I can be prepared by reacting a diazonium compound of an amine of the formula ##STR7## with a coupling component of the formula
KH
by a conventional method.
The Examples which follow illustrate the preparation. Parts and percentages are by weight, unless stated otherwise.
Of particular importance are compounds of the formula Ia ##STR8## where B1 is C1 -C8 -alkyl, B2 is acyl and K1 is a radical of a coupling component from the aniline or thiazole series.
Preferred coupling components K1 H are: ##STR9##
11.9 parts of 5-amino-4-cyano-3-β-[N,N-acetylethylamino]-ethylisothiazole were dissolved in 75 parts by volume of a mixture of 17 parts of glacial acetic acid and 3 parts of propionic acid. 20 parts of 85% strength sulfuric acid were added, after which 16 parts of nitrosylsulfuric acid (11.5% of N2 O3) were run slowly into the stirred solution at 0°-5° C., and stirring was continued at the same temperature for 4 hours. The resulting diazonium salt solution was run slowly into a mixture of 12.8 parts of 4-phenyl-2-(N-diallylamino)-thiazole, 20 parts of acetic acid, 250 parts of water, 250 parts of ice and one part of amidosulfonic acid. When coupling was complete, the dye was filtered off under suction, washed neutral and dried at 50° C. under reduced pressure to give 18.0 parts of the dye of the formula ##STR10## This dye dyes polyesters in deep violet hues which have good lightfastness and fastness to dry heat pleating and setting.
The dyes characterized in the Table below by diazo and coupling components are also obtained similarly to Example 1.
__________________________________________________________________________
Ex- Hue on
ample
Diazo component Coupling component polyesters
__________________________________________________________________________
##STR11##
##STR12## violet
3 "
##STR13## violet
4 "
##STR14## violet
5 "
##STR15## navy
6 "
##STR16## blue
7 "
##STR17## blue
8 "
##STR18## blue
9 "
##STR19## blue
10 "
##STR20## blue
11
##STR21##
##STR22## blue
12 "
##STR23## blue
13 "
##STR24## blue
14 "
##STR25## blue
15 "
##STR26## blue
16 "
##STR27## navy
17
##STR28##
##STR29## violet
18
##STR30##
##STR31## violet
19
##STR32## " violet
20
##STR33## " violet
21
##STR34##
##STR35## navy
22
##STR36## " navy
23
##STR37## " navy
24
##STR38##
##STR39## blue
25
##STR40## " blue
26
##STR41## " blue
27
##STR42##
##STR43## blue
28
##STR44## " blue
29
##STR45## " blue
30
##STR46## " blue
31
##STR47## " blue
32
##STR48## " blue
33
##STR49## " blue
__________________________________________________________________________
5.0 parts of 5-amino-4-cyano-3-(2'-N-ethyl- N-propionylamino)-ethylisothiazole in a mixture of 22.5 parts by volume of acetic acid and 7.5 parts by volume of propionic acid were stirred. 10 parts by volume of an 85% strength sulfuric acid were added, after which 6.4 parts of nitrosylsulfuric acid (11.5% of N2 O3) were run slowly into the stirred solution at 0°-5° C. and stirring was continued at the same temperature for 4 hours. The resulting diazonium salt solution was run slowly into a solution of 3.9 parts of N-cyanoethyl-N-ethyl-m-toluidine in a mixture of 50 parts of water, 200 parts of ice, 10 parts by volume of 32% strength hydrochloric acid, 20 parts by volume of dimethylformamide and 0.5 part of amidosulfonic acid. When coupling was complete, the dye was filtered off under suction, washed neutral and dried to give 9.2 parts of the dye of the formula ##STR50## This dye dyes polyester fibers in clear bluish red fast hues.
The compounds below can be prepared by a similar method.
__________________________________________________________________________
Hue on
Example
Diazo component Coupling component polyesters
__________________________________________________________________________
35
##STR51##
##STR52## red
36
##STR53##
##STR54## red
37
##STR55##
##STR56## red
38
##STR57##
##STR58## red
39
##STR59##
##STR60## red
40
##STR61##
##STR62## red
41
##STR63##
##STR64## red
42
##STR65##
##STR66## red
43
##STR67##
##STR68## red
44
##STR69##
##STR70## red
45
##STR71##
##STR72## red
46
##STR73##
##STR74## red
47
##STR75##
##STR76## red
48
##STR77##
##STR78## reddish violet
49
##STR79##
##STR80## reddish violet
50
##STR81##
##STR82## red
51
##STR83##
##STR84## red
52
##STR85##
##STR86## reddish violet
53
##STR87##
##STR88## red
54
##STR89##
##STR90## red
55
##STR91##
##STR92## red
56
##STR93##
##STR94## red
57
##STR95##
##STR96## red
58
##STR97##
##STR98## red
59
##STR99##
##STR100## reddish violet
60
##STR101##
##STR102## reddish violet
61
##STR103##
##STR104## red
62
##STR105##
##STR106## reddish violet
63
##STR107##
##STR108## red
64
##STR109##
##STR110## red
65
##STR111##
##STR112## red
66
##STR113##
##STR114## red
67
##STR115##
##STR116## red
68
##STR117##
##STR118## red
69
##STR119##
##STR120## red
70
##STR121##
##STR122## red
71
##STR123##
##STR124## red
72
##STR125##
##STR126## red
73
##STR127##
##STR128## red
74
##STR129##
##STR130## red
75
##STR131##
##STR132## red
76
##STR133##
##STR134## red
77
##STR135##
##STR136## red
78
##STR137##
##STR138## red
79
##STR139##
##STR140## red
80
##STR141##
##STR142## red
81
##STR143##
##STR144## red
82
##STR145##
##STR146## red
83
##STR147##
##STR148## red
84
##STR149##
##STR150## red
85
##STR151##
##STR152## red
86
##STR153##
##STR154## red
87
##STR155##
##STR156## red
88
##STR157##
##STR158## red
89
##STR159##
##STR160## red
90
##STR161##
##STR162## red
91
##STR163##
##STR164## red
92
##STR165##
##STR166## red
93
##STR167##
##STR168## red
94
##STR169##
##STR170## red
95
##STR171##
##STR172## red
96
##STR173##
##STR174## red
97
##STR175##
##STR176## red
98
##STR177##
##STR178## red
99
##STR179##
##STR180## red
100
##STR181##
##STR182## red
101
##STR183##
##STR184## red
102
##STR185##
##STR186## red
__________________________________________________________________________
6 parts of 5-amino-4-cyano-3-[2-(N-acetyl-N-ethylamino)-ethyl]-isothiazole were introduced into 35 parts of a 3:1 mixture of glacial acetic acid and propionic acid. 15 parts of 85% strength sulfuric acid were added, after which 8 parts of nitrosylsulfuric acid (11.5% of N2 O3) were added dropwise at 0°-5° C., and stirring was continued for 4 hours at this temperature.
6.6 parts of N-ethyl-N-(2-propylaminocarbonyloxy)ethyl-m-toluidine were suspended in 10 parts by volume of 30% strength hydrochloric acid, 0.3 part of a fatty alcohol oxyethylate and 120 parts of water. 130 parts of ice were added, after which the diazonium salt solution was run in. When coupling was complete, the resulting dye suspension was filtered, and the filter cake was washed neutral with water and dried at 50° C. under reduced pressure to give 8 parts of the dye of the formula ##STR187## This dye dyes polyesters in clear violet hues.
__________________________________________________________________________
DNNK
Ex- Hue on
ample
Diazo component Coupling component polyesters
__________________________________________________________________________
104
##STR188##
##STR189## red
105 "
##STR190## red
106 "
##STR191## red
107 "
##STR192## red
108 "
##STR193## red
109 "
##STR194## red
110 "
##STR195## red
111 "
##STR196## red
112 "
##STR197## red
113 "
##STR198## red
114 "
##STR199## violet
115
##STR200##
##STR201## red
116 "
##STR202## violet
117
##STR203##
##STR204## red
118 "
##STR205## red
119 "
##STR206## red
120 "
##STR207## red
121
##STR208##
##STR209## blue
122 "
##STR210## red
123 "
##STR211## red
124 "
##STR212## red
__________________________________________________________________________
Claims (4)
1. A compound of the formula: ##STR213## where R is hydrogen, C1 -C4 -alkyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl or nitrophenyl; R1 is allyl, C1 -C8 -alkyl, C1 -C8 -alkyl substituted by C1 -C8 -alkoxy, phenoxy, phenyl or C1 -C8 -alkanoyloxy, cyclopentyl, cyclohexyl, and methylcyclohexyl, norbornyl, phenyl or phenyl substituted by chlorine, methyl or alkoxy; R2 is C1 -C10 -alkanoyl, C1 -C10 -alkanoyl substituted by alkoxy or phenoxy, cyclohexanoyl, benzoyl, benzoyl substituted by chlorine, methyl or methoxy, C1 -C8 -alkoxycarbonyl, aminocarbonyl, phenylaminocarbonyl, CH3 NHCO, C2 H5 NHCO, C3 H7 NHCO, C4 H9 NHCO, (CH3)2 NCO, CH3 SO2, C6 H5 SO2 or p--CH3 --C3 H4 --SO2 ; or R1 and R2, together with the nitrogen atom, form a ring system selected from the group consisting of: ##STR214## and K is a radical of a coupling component.
2. The compound as claimed in claim 1, wherein KH is of the formula: ##STR215## where R3 is hydrogen, alkyl, aralkyl or aryl, R4 is hydrogen or R5, where R5 is C1 -C6 -alkyl, or C1 -C6 -alkyl substituted by chlorine, bromine, hydroxyl, C1 -C8 -alkoxy, phenoxy, cyano, carboxyl, C1 -C8 -alkanoyloxy, C1 -C8 -alkoxy-C1 -C4 -alkoxy, benzoyloxy, o-, m- or p-methylbenzoyloxy, o-, m- or p-chlorobenzoyloxy, C1 -C8 -alkoxyalkanoyloxy, phenoxyalkanoyloxy, C1 -C8 -alkoxycarbonyloxy, C1 -C8 -alkoxyalkoxycarbonyloxy, benzyloxycarbonyloxy, phenethyloxycarbonyloxy, phenoxyethoxycarbonyloxy, C1 -C8 -alkylaminocarbonyloxy, cyclohexyl-aminocarbonyloxy, phenylamino-carbonyloxy, C1 -C8 -alkoxy-carbonyl, C1 -C8 -alkoxyalkoxy-carbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenoxy-C1 -C4 -alkoxy or phenethyloxycarbonyl, or phenyl, benzyl, phenethyl or cyclohexyl, R6 and R7 are each hydrogen, alkyl, alkoxy, phenoxy, halogen, alkylsulfonylamino, dialkylaminosulfonylamino, benzyloxy, benzylamino or C1 -C6 -alkanoylamino, R8 is cyano, carbamyl, nitro or carbalkoxy, and R9 is C1 -C4 -alkyl, C1 -C4 -alkoxycarbonylmethyl, cyanomethyl, benzyl or phenyl which is monosubstituted or polysubstituted by C1 -C10 -alkyl, C1 -C10 -alkoxy, phenoxy, benzyloxy, phenyl, chlorine, bromine, nitro, C1 -C4 -alkoxycarbonyl, C1 -C4 -mono- or di-alkylamino, C1 -C4 -alkoxyethoxy, C1 -C4 -alkyl- or phenyl-mercapto.
3. The compound as claimed in claim 2, wherein said R5 substituent is methyl, ethyl, propyl, butyl, pentyl, hexyl, allyl, methallyl, 2-chloroethyl, 2-bromoethyl, 2-cyanoethyl, 2-hydroxyethyl, 2-phenyl-2-hydroxyethyl, 2,3-dihydroxypropyl, 2-hydroxy-propyl, 2-hydroxy-butyl, 2-hydroxy-3-phenoxypropyl, 2-hydroxy-3-methoxypropyl, 2-hydroxy-3-butoxypropyl, 3-hydroxypropyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-butoxyethyl, 2-phenoxyethyl, 2-phenoxypropyl, 2-acetoxyethyl, 2-propionyloxyethyl, 2-butyryloxyethyl, 2-isobutyryloxyethyl, 2-methoxymethylcarbonyloxyethyl, 2-ethoxymethylcarbonyloxyethyl, 2-phenoxymethylcarbonyloxyethyl, 2-methoxycarbonyloxyethyl, 2-ethoxycarbonyloxyethyl, 2-propoxycarbonyloxyethyl, 2-butoxycarbonyloxyethyl, 2-phenyloxycarbonyloxyethyl, 2-benzyloxycarbonyloxyethyl, 2-methoxyethoxycarbonyloxyethyl, 2-ethoxyethoxycarbonyl-oxyethyl, 2-propoxyethoxycarbonyloxyethyl, 2-butoxyethoxycarbonyloxyethyl, 2-methylaminocarbonyl-oxyethyl, 2-ethyl-aminocarbonyloxyethyl, 2-propylaminocarbonyloxyethyl, 2-butylaminocarbonyloxyethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 2-propoxycarbonylethyl, 2-butoxycarbonylethyl, 2-phenoxycarbonylethyl, 2-benzyloxycarbonyl-ethyl, 2-β-phenyloxycarbonylethyl, 2-methoxyethoxycarbonylethyl, 2-ethoxyethoxycarbonylethyl, 2-propoxyethoxycarbonylethyl, 2-butoxyethoxycarbonylethyl or 2-phenoxyethoxycarbonylethyl.
4. A compound of the formula: ##STR216## where R is hydrogen, C1 -C4 -alkyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl or nitrophenyl; R1 is methyl, ethyl, propyl, butyl, hexyl, octyl, C2 H5 -OCH2 CH2, CH3 OCH2 CH2 CH2 --, C4 H9 OCH2 CH2 CH2 --, C6 H5 OCH2 CH2 --, C6 H5 OCH2 CH2 OCH2 CH2 CH2 --, C6 H5 CH2 -- or C6 H5 CH2 CH2 --; R2 is C1 -C10 -alkanoyl C1 -C10 -alkanoyl substituted by alkoxy or phenoxyl, cyclohexanoyl, benzoyl, benzoyl substituted by chlorine, methyl or methoxy, C1 -C8 -alkoxycarbonyl, aminocarbonyl, phenylaminocarbonyl, CH3 NHCO, C2 H5 NHCO, C3 H7 NHCO, C4 H9 NHCO, (CH3)2 NCO, CH3 SO2, C6 H5 SO2 or p--CH3 --C6 H4 --SO2 ; or R1 and R2, together with the nitrogen atom, form a ring system selected from the group consisting of: ##STR217## and K is a radical of a coupling component.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3409243 | 1984-03-14 | ||
| DE19843409243 DE3409243A1 (en) | 1984-03-14 | 1984-03-14 | ISOTHIAZOLAZO DYES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4619992A true US4619992A (en) | 1986-10-28 |
Family
ID=6230405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/710,993 Expired - Fee Related US4619992A (en) | 1984-03-14 | 1985-03-12 | 3-(β-aminoethyl)-4-cyano-isothiazolylazo dyes |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4619992A (en) |
| EP (1) | EP0156216B1 (en) |
| JP (1) | JPS60228567A (en) |
| DE (2) | DE3409243A1 (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4820809A (en) * | 1984-07-24 | 1989-04-11 | Basf Aktiengesellschaft | Heterocyclic azo dyes |
| US4960873A (en) * | 1988-03-29 | 1990-10-02 | Basf Aktiengesellschaft | 3-pyridylisothiazoleazo compounds useful as disperse dyes |
| US5132412A (en) * | 1988-10-01 | 1992-07-21 | Basf Aktiengesellschaft | Thiazoleazo dyes having a diazo component from the isothiazole or thiadiazole series |
| US5216139A (en) * | 1988-10-01 | 1993-06-01 | Basf Aktiengesellschaft | Thiopheneazo dye based on a coupling component of the thiazole series |
| US5825652A (en) * | 1995-09-08 | 1998-10-20 | Gerber Garment Technology, Inc. | Sample garment making system |
| US6187084B1 (en) * | 1998-03-31 | 2001-02-13 | Zeneca Ltd. | Ink compositions |
| US6197223B1 (en) | 1996-11-27 | 2001-03-06 | Eastman Chemical Company | Method for preparing light-absorbing polymeric compositions |
| WO2010143745A1 (en) * | 2009-06-10 | 2010-12-16 | Fujifilm Corporation | Colored curable composition, color resist, ink-jet ink, color filter and method for producing the same, solid-state image pickup device, image display device, liquid crystal display, organic el display, and colorant compound and tautomer thereof |
| US20110117337A1 (en) * | 2008-07-11 | 2011-05-19 | Fujifilm Imaging Colorants Limited | Magenta Dyes and Inks for Use in Ink-Jet Printing |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1975204B1 (en) * | 2007-03-27 | 2013-10-02 | FUJIFILM Corporation | Azo dye and azo compound |
| JP2010001455A (en) | 2008-03-07 | 2010-01-07 | Fujifilm Corp | Azo pigment, pigment dispersion and coloring composition, containing the azo pigment |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2041391A (en) * | 1979-01-30 | 1980-09-10 | Sandoz Ltd | Improvements in or relating to monoazo dyes |
| US4324899A (en) * | 1979-07-05 | 1982-04-13 | Eastman Kodak Company | 2-Amino-5-cyanothiazoles and their preparation |
| EP0087677A1 (en) * | 1982-02-27 | 1983-09-07 | BASF Aktiengesellschaft | Isothiazolazo dyestuffs |
| EP0087616A1 (en) * | 1982-02-16 | 1983-09-07 | BASF Aktiengesellschaft | Isothiazolazo dyestuffs |
| US4500718A (en) * | 1981-04-06 | 1985-02-19 | Ciba-Geigy Corporation | Process for producing bismethine isoindolines |
| EP0135131A1 (en) * | 1983-08-20 | 1985-03-27 | BASF Aktiengesellschaft | Azo dyestuffs of the isothiazole series |
-
1984
- 1984-03-14 DE DE19843409243 patent/DE3409243A1/en not_active Withdrawn
-
1985
- 1985-03-07 EP EP85102574A patent/EP0156216B1/en not_active Expired
- 1985-03-07 DE DE8585102574T patent/DE3560583D1/en not_active Expired
- 1985-03-12 JP JP60047616A patent/JPS60228567A/en active Pending
- 1985-03-12 US US06/710,993 patent/US4619992A/en not_active Expired - Fee Related
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2041391A (en) * | 1979-01-30 | 1980-09-10 | Sandoz Ltd | Improvements in or relating to monoazo dyes |
| US4324899A (en) * | 1979-07-05 | 1982-04-13 | Eastman Kodak Company | 2-Amino-5-cyanothiazoles and their preparation |
| US4500718A (en) * | 1981-04-06 | 1985-02-19 | Ciba-Geigy Corporation | Process for producing bismethine isoindolines |
| EP0087616A1 (en) * | 1982-02-16 | 1983-09-07 | BASF Aktiengesellschaft | Isothiazolazo dyestuffs |
| EP0087677A1 (en) * | 1982-02-27 | 1983-09-07 | BASF Aktiengesellschaft | Isothiazolazo dyestuffs |
| US4496480A (en) * | 1982-02-27 | 1985-01-29 | Basf Aktiengesellschaft | Isothiazolazo dyes having coupling components which are free from unsaturated aliphatic radicals |
| EP0135131A1 (en) * | 1983-08-20 | 1985-03-27 | BASF Aktiengesellschaft | Azo dyestuffs of the isothiazole series |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4820809A (en) * | 1984-07-24 | 1989-04-11 | Basf Aktiengesellschaft | Heterocyclic azo dyes |
| US4960873A (en) * | 1988-03-29 | 1990-10-02 | Basf Aktiengesellschaft | 3-pyridylisothiazoleazo compounds useful as disperse dyes |
| US5132412A (en) * | 1988-10-01 | 1992-07-21 | Basf Aktiengesellschaft | Thiazoleazo dyes having a diazo component from the isothiazole or thiadiazole series |
| US5216139A (en) * | 1988-10-01 | 1993-06-01 | Basf Aktiengesellschaft | Thiopheneazo dye based on a coupling component of the thiazole series |
| US5825652A (en) * | 1995-09-08 | 1998-10-20 | Gerber Garment Technology, Inc. | Sample garment making system |
| US6197223B1 (en) | 1996-11-27 | 2001-03-06 | Eastman Chemical Company | Method for preparing light-absorbing polymeric compositions |
| US6776930B2 (en) | 1996-11-27 | 2004-08-17 | Eastman Kodak Company | Method for preparing light-absorbing polymeric compositions |
| US20040195552A1 (en) * | 1996-11-27 | 2004-10-07 | Weaver Max Allen | Method for preparing light-absorbing polymeric compositions |
| US6187084B1 (en) * | 1998-03-31 | 2001-02-13 | Zeneca Ltd. | Ink compositions |
| US20110117337A1 (en) * | 2008-07-11 | 2011-05-19 | Fujifilm Imaging Colorants Limited | Magenta Dyes and Inks for Use in Ink-Jet Printing |
| WO2010143745A1 (en) * | 2009-06-10 | 2010-12-16 | Fujifilm Corporation | Colored curable composition, color resist, ink-jet ink, color filter and method for producing the same, solid-state image pickup device, image display device, liquid crystal display, organic el display, and colorant compound and tautomer thereof |
| CN102405261A (en) * | 2009-06-10 | 2012-04-04 | 富士胶片株式会社 | Colored curable composition, color resist, ink-jet ink, color filter and method for producing the same, solid-state image pickup device, image display device, liquid crystal display, organic el display, and colorant compound and tautomer thereof |
| US8741508B2 (en) | 2009-06-10 | 2014-06-03 | Fujifilm Corporation | Colored curable composition, color resist, ink-jet ink, color filter and method for producing the same, solid-state image pickup device, image display device, liquid crystal display, organic el display, and colorant compound and tautomer thereof |
| CN102405261B (en) * | 2009-06-10 | 2014-10-15 | 富士胶片株式会社 | Colored curable composition, color resist, ink-jet ink, color filter and method for producing the same, solid-state image pickup device, image display device, liquid crystal display, organic EL display, and colorant compound and tautomer thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3560583D1 (en) | 1987-10-15 |
| EP0156216B1 (en) | 1987-09-09 |
| DE3409243A1 (en) | 1985-09-19 |
| EP0156216A1 (en) | 1985-10-02 |
| JPS60228567A (en) | 1985-11-13 |
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